Cal industry in basle



UNITED STATES PATENT OFFICE.

CAEBL JAGERSPAOHER, OF BASEL. SWITZERL GAL INDUSTRY IN BASLE, 0

AND. ASSIGNOR TO SOCIETY OF CHEMI- F BASEL, SWITZERLAND.

AZG DYESTUFFS DYEI NG ON MORDANTS.

No Drawing.

To all whom it may concern e it known that I CARI. Jnonnsmomm, a citizen of.the Swiss Republic, and resident of Basel, Switzerland, have invented new and useful Azo Dyestuffs Dyeing? on film" dents, of which the following is a full, clear, and exact specification.

his is a continuation in part of my eppli cation for Letters Patent filed May 14, 1919, Ser. No. 297095.

I have found that by combining aromatic orthooxydiazoeompounds with I :tiul egsynaphthalene'sulfocarboxylio acids, there are obtained new azodyestufi's dyeing on inordants which are particularly suitable for printing cotton with chromium mordants.

hese new azocl estufls eonstitute.-in :1 dry state, dark powders, which dissolve in water with red'vlolet to blue colorations and in concentrated sulfuric arid with violet to green-blue colorations, dye wool in an arid bath violet tints becoming, on subsequent chroming, fast blue to black. and produce fast blue to black prints, when printed on cotton with chromium mordants.

The manufarture of the new [:ti-dioxynaphthalenrsulforarhoxylic acids employed as parent materials and the nnuiufurture ol' the new azodyrstutl's derived from the said arids are illustrated by the following exumples:

avmrple 1.

Preparation of the I 8-rI1'o.-r 1 wn phi/I Merle-- 3-sulf0-6-e1ilrbrmy/ie arid-4W6 parts of naphthalene 5 :7 disulfo-2-rnrlmxylic acid (derived lfimm the rorrespondiug miphthylumino-disulfonie acid by Substituting :1 eyenogen-groupie! the amino group and subsequently. saponifying the ryunogen group) are finely groundnnd dissolved without cooling, in 1500mm of sulfuric :u-id of 65 B6. whereby the temperature rises to to i After cooling the solution down to 25 L, there are added 100 parts of uitrir arid of 40 B6. while stirrmg and rooling with water. The temperutlur rises up-to (7.

The clear, yellow nitruted mass is introdured into 4000 parts of water and rrdurvd by adding gradually 23 parts of iron filings at 25 to 45 C. he iron-sodium salt of the 1 am inonaphthulene 6: 8-disulf0-3-czu'hox- Specification of Letters Patent.

ylir acid, which Patented Apr. 26, 1921. Application filed November 15, 1919. Serial No. 338,848.

precipitates hereby, is sepcooled down, and converted in known manner into the rm'respomling this latter is rom'erted afterward into the corresponding d of the acid for t not necessary.

250 parts of tl toic soul in form cent, are ariditied with 12? truterl sulfuric temperature not sodium nitrite.

is partly separa ing. When no he detected, the of lime filtered pared with sodium oarhouutr.

lution separated formed hy filtration. the l isodium salt.

A separation he subsequent dinzotation is iis disulfonuted amiuonuphof neutral solution of 12 per )zu'ts of (Ontftnarid and d over 12 (1,

The diazoeompoum whirh ralrium-smlium salt and iazotizod, at a with 5!) mrtsof ted, is decomposed by ho-iL dmzorompound ra'u i'urther and the sodium salt is pro ralrium carbonate :fiumphthosulton- :u'ld does not have to he from the sr 'nu'uted. hut on the contrary it run-he employed dirertly prom-so after it nerossury degree of rom'entrution.

ronrontrutimi tl (300 parts by weight soda lye u re add mixture is host hours at 185 to l melted mass is idnnd the sulfur-nus ing. From the tion the l hoxylie acid crystallizes hrown crystals. and prrripitutin aoid is obtained. of sandy, yollo for has horn rourrntroted to the Toefiret 10 solution is evaporated to and 300 parts of solid ed thereto and the resulting ed in :m autorhu'e for 31} on" while stirring. :u'idilird with hydrorhlorir lly rrdissolviug in water o with romulon sultthenew in a pure state. in the form.

' precipitate. it ronstitutes u yellow Powder. and is readily soluble in hot water. lluorrsrene.

than-tho ohromo ts alkaline solution shows With dinzouoruioimds whirh easily 1 i zR-dioxyuaph-- u green tropir arid (l thuh-uel:ti-disulfouir arid).

if instead of the naphthalene-5 7-disulfosulfo-Q-mrhoxyl the naphthalenel-:H-diin acid (ohtuumhle from the mrresponding: unphthylamiudisulfonir arid) be employed as tamed in an an parent material, there is ohalogous manner the 1:8-di- From the so-' The i arid expelled hv hoilnearly saturated salt sol"; :H-dioxynuphlhalo|1v-3-s|dfo-ti-(rnl' 1 :la

in form of yellow umss is neutralized with milk oxynaphthalene 4 sulfo-G-carboxylic acid. his acid constitutes in a dry state a yellowbrown powder and is more easily soluble in water than the isomeric 1:8-dioxyna hthalene-3-sulfo-6-carboxylic acid. Its a slim solution shows a feeble blue-green fluorescence.

Ewmnple v18.7 parts of z-ammot-chloro-l-oxybenzene-(i-carboxylic acid are diazotized in known manner as concentrated as possible, and the resulting diazo compound 15 introduccd while stirring, into a mixture of 28.4 parts of 1 8-dioxynaphthalene-G-sulfo-3-carboxylic acid and 100 parts of milk of lime of 20 per cent. The combination bein cffected, the dyestufl' is separated by a ding hydrochloric acid, filtered off, dissolved in sodium carbonate, se arated by filtration from the calcium car onate formed salted out from the filtrate, separated by filtration and dried. The combination can also be carried outin an acetic solution.

The dyestufi' constitutes in a dry state, a blue-black powdcr, dissolving in water to red-violet solutions and in concentrated sulfuric acid with green-blue coloration. When printed on cotton with chromium mordunts, 1t ives blue prints fast to soaping, chlorin and light.

If instead of the 1:8-dioxynaphthalene-3- sulfo-6-curboxylic acid the isomeric 1:8-dioxynapl1thalene-4-sulfo-(i-carboxylic acid is employed there results a similar somewhat redder dyestufi.

Example 3.

The diazo-com and derived from 16 parts of 2-amino-tlfiitro-4-methyl-l-oxybenzone and prepared as concentrated as possible is united with a suspension of 28.4 parts of 1 :8-dioxynaphthalene-6-su]fo 3 carbon-Q ylic acid in 100 parts of milk of lime of 2d per cent. The combination-being etlected, the reaction mass is acidified with hydro chloric acid, the separated dyestutl 1s dissolved with sodium carbonate, the solution of the dyestufl' so arated m the calcium carbonate formed filtrat on, the dgeistnfl salted out from the filtrate, separa 3 by filtration and dried. I

The dyestuficonstitutes, n a dry state, a blue-black powd dissolving, in water to violetsolutions nail in concentrated sulfuric acid to blue solutions. It dyes wool, in an acid bath, violet tints turning, on subse quent chromin to a blue fast to fulhng, potting and ii t; when printed on cotton with chromium mordants, it ves blue prints fast to soaping, chlonn an 1: t.

It instead of the 1: 8 d1oxynaphtha ens-2}- sulfo-fl-carboxylic acid the isomeric 1:8-d1- oxynafihthalcnc-issulfo-G-carboxylic acid is empio ed there is obtained a similar, somewhat I dder dyestufl'.

Ewample 4.

The diam-compound derived from 19.? parts of 2-amino-3:ti-dinitro-l-oxybenzene and prepared as concentrated as 'ible is united with a suspension of 28. parts of 1 B-dioxynaphthalene-G-sulfo 3 carboxylic acid in 100 parts of milk of lime of 20 per cent. The combination bein effected, the reaction mass is acidified Witfi hydrochloric acid, the se arated dvestufl' is dissolved with sodium ca ate, the solution of the dyestufi' separated from the calcium carbonate formed by filtration, the dyestufl' salted out. fron the filtrate, separated by filtration'ajnd The dyestufi' constitutes, y a dark brown powder, dissolving in; water to violet solutions and in concentrated sulfuric acid to violet solutions. Itfdyes wool, 1n an acid bath, blue-black tints turning, on sub uent chroming, to an olive reen fast to lling, potting and light. "hen printed on cotton with chromium mordants, it gives black prints fast an light.

What I claim is: 1. As new roducts, the herein described azodyestufl's yeing on moi-(hints, derived from aromatic 'orthooxy-diuzo-com umls and 1:B-dioxynaphthalene-sulfocar x -'lic i a ry to Scoping, chiorin acids, which constitute, in El, dry state, b ack to darlr brown powders dissolving in water with violet colorations and in concentrated sulfuric acid with violet to green-blue col orations, d e wool in an acid bath red brown to blue-vio et tints becoming on subsequent chroming, fast blue and olive to black and produce, when printed on cotton with chromiumAmoi-dants, fast blue to black tints. 2.

s a new article of manufacture the herein described azodyestuif dyeing on mordants, derived from 2-diazo-6-nitro-4- methyl-l-oxybenzene and lzfi-dioxynapln thalene-li-sulfo-fi-carboxylic acid. which constitutes, in a dry state, a bluebluck powder, dissolving in water to a violet and in concentrated sulfuric acid to a blue solution,

dyes wool inan acid bath, violet tints turnin'g, on so uent chroming. to a blue fast to falling an to potting and gives, when rinted on cotton with chromium moi-dents, lue tints fast to soaping, chlorin audlight. In witness whereof I have hereunto signed my name this 28th da of October 1919, in

the presence of two so ribin witnesses. CARL JAGER ACHER. Witnesses;

H. H, DICK, hum) Rm'sa. 

